Resonance Structures, Two valid Lewis structures can be drawn for the ion, 2 3 - - resonance structures - F = 6 Resonance structures: -6 Lewis structures that -1/2(2) differ only in the placement of electrons -1
Resonance Structures 2-3 exists as a resonance hybrid a substance that requires 2 or more resonance structures to adequately, represent it properties of the substance are a blend of all possible resonance structures - -
Resonance Structures The negative charge on 2-3 is delocalized over both the carbon and oxygen spread out over two or more atoms by resonance harge delocalization makes 2-3 more stable It is resonance stabilized because the charge can be spread out over 2 or more atoms -, -
Drawing Resonance Structures Rules for drawing resonance structures: All resonance structures must be valid Lewis structures,, nly electrons can be moved around nuclei cannot be moved - Resonance stabilization - is most important when it helps delocalize a charge over two or more atoms Are these resonance structures?
Resonance Structures To convert from one resonance structure to another: move nonbonding electrons or pi electrons towards either: a positive charge an adjacent pi bond a more electronegative atom Remember, the electrons move The charge is delocalized (and moves to a new atom) as a result of the electrons moving
Resonance Structures, urved arrows are commonly used to show the movement of electrons when converting from one resonance structure to another Arrow begins at the electron pair that is moving - -
- Resonance Structures Example: Draw all possible major resonance structures for the following - + - 2 3 3 F = 6-6 -1/2(2) -1 F = - 6-6 + + 2-3 + 2 - + F = 6-6 -1/2(2) -1 -
Resonance Structures The resonance structures for a particular substance sometimes have different energy and stability Major contributor: the more stable resonance structure lower energy has the greatest influence on the properties and behavior of the resonance hybrid Minor contributor the less stable resonance structure higher energy
Resonance Structures A resonance hybrid most strongly resembles the lowest energy resonance structure (major contributor) Lewis structure of the major contributor is characterized by: as many octets as possible as many bonds as possible negative charge on the most electronegative atom as little charge separation as possible
Resonance Structures Example: onsider the following two resonance structures for 3 2+ Which one is the major contributor?
3-Dimensional Drawings VSEPR can be used to determine the electron domain and molecular geometries around any main group atom Draw the Lewis structure ount the number of electron domains Assign the geometry 2 ed = 3 ed = 4 ed =
A A 3-Dimensional Drawings You must also be able to draw an appropriate 3-dimensional structure for A organic molecules E B A D E B B D B In the plane of B the slide A B A B B B A B B B Trigonal planar B tetrahedral Going back and away from you oming out toward you
3-Dimensional Drawings Example: Draw a 3-dimensional drawing of acrylic acid, 2 = 2
3-Dimensional Drawings Example: Draw a 3-dimensional structure for acetone
ondensed Structural Formulas ondensed structural formula each central atom is shown with the atoms that are bonded to it atoms bonded to the central atom are usually listed after the central atom Put substituents in parentheses two or more identical groups are shown in parentheses with a subscript to indicate quantity the bonds between atoms are usually not shown exception: double and triple bonds between two carbons should be shown
ondensed Structural Formulas Examples: 3 2 3 3 2 3 3 () 2 ( 3 ) 2 3 () 2 ( 3 ) 2 3 3 2 3 Br Br 3 (Br) 2 2 3
Line Angle Drawings Line-angle formula or drawing bonds are represented by lines carbon atoms are present: where a line begins or ends (if no other atom is shown at the end of the line) where two lines meet eteroatoms like N,, S and halogen atoms are always shown Aldehyde hydrogens are always shown ther hydrogens are shown only if attached to an atom that has been drawn using its elemental symbol
Line Angle Drawings Examples: 3 3 3 2 2 2 3-2 R where R = alkyl group 3 2 2 2 3-2 R where R = alkyl group 3 () 2 ( 3 ) 2 3 () 2 ( 3 ) 2
Line Angle Drawings Line angle drawings are intended to show 3-d structure ommon errors: incorrect correct incorrect correct Alkynes are linear, not tetrahedral or trigonal planar Substituents on a tetrahedral are ~1095 o apart, not 180 o as this drawing shows
hemical Formulas Example: Draw the condensed structural formula and the line angle drawing for: 3 3
hemical Formulas Example: Draw the condensed structural formula for Br Br N